Sodium Carbonate → N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a 10-mL, round-bottomed flask was added N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide from Step 4 (0.060 g, 0.28 mmol), 4-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (0.19 g, 0.51 mmol, Aldrich, St. Louis, Mo.), DMF (3.0 mL), and aq. sodium carbonate (0.85 mL, 1.7 mmol, 2 M). The mixture was carefully evacuated and backfilled with N2. Bis(triphenylphosphine)palladium(II) chloride (20 mg, 0.028 mmol, Strem Chemical, Inc., Newburyport, Mass.) was added. Once again, the mixture was carefully evacuated and backfilled with N2. The mixture was stirred at 100° C. for 2 h and then allowed to cool to room temperature. The mixture was poured into water (75 mL) and extracted with EtOAc (3×75 mL). The combined extracts were washed with water (2×50 mL) and brine (50 mL) then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as an off-white solid. MS (ESI positive ion) m/z: 422 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.92 (s, 1H), 10.44 (s, 1H), 8.26 (s, 1H), 8.05 (d, J=9.6 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.67-7.71 (m, 3H), 7.61 (d, J=9.6 Hz, 1H), 7.40 (t, J=7.9 Hz, 1H), 7.35 (d, J=8.0 Hz, 2H), 7.19 (dd, J=8.0 Hz, 1.4 Hz, 1H), 2.32 (s, 3H), 2.11 (s, 3H).

Provenance & Evidence